Synthesis and characterization of alkyl- and acyl-substituted oxime–phosphazenes

Two oxime–cyclophosphazenes were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene ( 2 ) and hexakis(4-acetylphenoxy)cyclotriphosphazene ( 8 ). The reactions of these oximes with ethyl bromide, allyl bromide, propanoyl chloride, and acriloyl chloride were studied. Hexasubstituted compounds were obtained from the reactions of hexakis{4-[(hydroxyimino)methyl]phenoxy}cyclotriphosphazene ( 3 ) with ethyl bromide ( 4 ), allyl bromide ( 5 ), and propanoyl chloride ( 6 ), however, the oxime groups on 3 rearranged to nitrile ( 7 ) in the reaction of 3 with acriloyl chloride. Hexasubstituted compounds were also obtained from the reactions of hexakis{4-[(1)-N-hydroxyethaneimidoyl]phenoxy}cyclotriphosphazene ( 9 ) with allyl bromide ( 11 ) and propanoyl chloride ( 12 ). Tetra- and penta-substituted products were obtained from the reactions of 9 with ethyl bromide ( 10 ) and acriloyl chloride ( 13 ), respectively. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, IR, 1 H, 13 C, and 31 P NMR spectroscopy. Key words: hexachlorocyclotriphosphazene, phosphazene, oxime, oxime derivatives, oxime–phosphazenes.